Intramolecular Diels-Alder reaction with an α-methylene lactone as dienophile

Synlett

Volumn , Issue 2, 1998, Pages 159-160

  Maier, Martin E ^a   Perez, Caroline ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002898455     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1593     Document Type: Article

References (16)

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3. For some representative examples, see: (a) Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390-4392.
4. (b) Lu, Y.-F.; Fallis, A. G. Can. J. Chem. 1995, 73, 2239-2252.
5. (c) Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 7508-7512.
6. (d) Wong, T.; Wilson, P. D.; Woo, S.; Fallis, A. G. Tetrahedron Lett. 1997, 38, 7045-7048.
7. Hoffmann, H. M. R.; Rabe, J. Angew. Chem. 1985, 97, 96-112;
8. Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
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11. Fürstner, A. Synthesis 1989, 571-590.
12. Villieras, J.; Rambaud, M. Synthesis 1982, 924-926.
13. Hanessian, S.; Park, H.; Yang, R.-Y. Synlett 1997, 351-352.
14. 1,6]dodec-4-en-11-one (5a,b): A solution of crude 4 (ca. 5.89 mmol) in toluene (60 ml) was heated in a sealed tube for 36 h at 110°C.
15. Hoye, T. R.; Hanson, P. R.; Vyvyan, J. R. J. Org. Chem. 1994, 59, 4096-4103.
16. PC model (V 4.0) from Serena Software was used. The calculations for the Diels-Alder transition states were performed as described in the manual (bond order = 0.3 for the newly formed sigma bond).